1. Ch. 13 Hydrocarbons
Milbank High School

2. Objectives
1. What is organic chemistry? In general, how do organic compounds differ from inorganic compounds?
2. Why are there so many more organic compounds than inorganic compounds?
3. What are hydrocarbons? What structural features identify alkanes? Alkenes? Alkynes? Aromatic hydrocarbons?
4. How are alkanes, alkenes, alkynes, and aromatic hydrocarbons named using IUPAC nomenclature?
5. What are the physical and chemical properties of alkanes, alkenes, alkynes, and aromatic hydrocarbons?

3. Objectives 6. What is an alkyl group?
7. What are some products from reactions of alkanes? How are they formed?
8. What are the major reactions of alkenes? What are the products of those reactions?
9. What are polymers? How are they formed and utilized?
10. What is petroleum and how is it utilized?

4. Organic Chemistry Chemistry of compounds that contain carbon
Combine mainly with hydrogen, oxygen, and nitrogen
Over 10 million compounds made with these 4 elements
95% of compounds contain carbon
Form stable, covalent bonds with each other

5. Properties Organic (Benzene) Inorganic (NaCl) Low melting pts
Low boiling pts
Low solubility in water
Highly flammable
Nonconductive
Covalent bonds
Inorganic (NaCl)
High melting pts
High boiling pts
Soluble in water
Nonflammable
Conductive
Ionic bonds

6. Hydrocarbons Compounds containing only two elements
Carbon and hydrogen
          
               

7. Sec. 13.1 Alkanes: Structures and Names
Objectives
Identify an alkane
Determine what an isomer of an alkane is
Identify different types of alkanes

8. Alkanes Saturated Hydrocarbons
Called saturated because each carbon is bonded to four other atoms
Only single bonds
Methane
Ethane
Propane

9. Homology Related compounds Homologs
Have properties that vary in a regular and predictable manner
A manner of organization
Similar to P.T.

10. Isomers Different compounds having the same molecular formula Butane
Isobutane (isolated branched chain)

11. Isomers
Pentane
Isopentane
Neopentane
                           
                      
                   

12. Alkanes CnH2n+2 Representation Structural Formulas
Condensed Structural Formulas
Butane

13. Alkyl Group
A group of atoms that results when one hydrogen atom is removed from an alkane
CnH2n+1
Change –ane ending to –yl
Methyl
Ethyl
Propyl

14. Sec. 13.2 IUPAC Nomenclature
Define IUPAC
Examine the rules for IUPAC naming
Determine the correct names of alkanes

15. IUPAC Nomenclature Geneva, Switzerland 1892
International Union of Pure and Applied Chemistry
IUPAC System of Nomenclature
(isobutane, isopentane are common names)

16. IUPAC Rules
1. Name the longest chain in the parent compound. End in –ane. (Root name)
Number each carbon
See Example
2. Note the alkyl groups attached
3. Number the carbon that the group is attached to.
Must use the lowest number possible.

17. IUPAC Rules Con’t
4. Use prefixes to indicate the amount of attached groups
See Example
5. If there are more than two or more different substituents, list them in alphabetical order. If at equal points, lower alphabetical order given lowest number

18. IUPAC Rules Con’t 6. Prefixes not included in alphabetizing
See Example

19. Name each of the following

20. Name each of the followingB. C. D.

21. Answers a. 3-ethylhexane 2,4-dimethylpentane c. 3-methylhexane
d. 4-isopropylheptane

22. Draw the structural formulas for each of the following
4-propylheptane
3-ethyl-2-methylpentane
3-isopropyl-3-methyloctane

23. Answers

24. Sec. 13.3 Properties of Alkanes
Objectives
Determine the physical and physiological properties of alkanes

25. Physical Properties Nonpolar Less dense than water
Insoluble in water
Less dense than water
Less than 1.0g/ml
Related to one another
See chart
Boiling points
Increase with higher molar mass

26. Physiological Properties
Gases serve as anesthetics
Liquid alkanes
Light liquids
Harmful to lungs
Heavy liquids
Mineral oil
Petroleum jelly

27. Sec. 13.4 Chemical Properties: Reactions of Alkanes
Objectives
Determine the chemical properties of alkanes

28. Chemical Properties Do not react with many laboratory agents
Usually very flammable
Undergo combustion reactions
CH4 + 2 O2  CO2 + 2 H2O + Heat
2 CH O2  2 CO + 4 H2O
(Harmful carbon monoxide reaction)
       
               
   

29. Sec. 13.5 Halogenated Hydrocarbons
Objectives
Define what halogenated hydrocarbons are
Name halogenated hydrocarbons using common and IUPAC names

30. Halogenated Hydrocarbons
Have one or more hydrogen atoms replaced by halogen atoms
Usually these are formed under UV light or very high temps
Results in an alkyl halide
           
                   
                     

31. Common Names First part of name is alkyl group
Second part is the halogen, ending in –ide
Name these:
CH3CH2Br
(CH3)2CHCl
CH3I
CH3CH2CH2F

32. Answers
Ethyl bromide
Isopropyl chloride
Methyl iodide
Propyl flouride

33. IUPAC Names Rules similar to those used for naming alkanes
Substitute in the prefixes fluoro-, chloro-, bromo-, and iodo-

34. Give the IUPAC name for each of the following compounds

35. Answers 2-chloropentane 4-bromo-2-methylhexane 2-chloro-3-methylbutane
1-bromo-3-chloro-4-methylpentane

36. Sec. 13.6 Cycloalkanes Define what a cycloalkane is
Name and draw cycloalkanes

37. Cycloalkanes Carbon atoms that are joined in a ring or circle
Simplest: cyclopropane
Another: cyclohexane

38. Naming Add cyclo- Otherwise fairly similar to regular naming
Draw structures for the following compounds
Cyclooctane
Ethylcyclohexane
1,1,2-trimethylcyclobutane

39. Answers A. B. C.

40. Draw these structures Cyclopentane 1-ethyl-2-methylcyclopentane
1-ethyl-1,2,5,5-tetramethylcycloheptane

41. Answers A. B. C.

42. Sec. 13.7 Alkenes Objectives Define alkene
Name alkenes using IUPAC rules

43. Alkenes End in -ene Unsaturated hydrocarbons
Have a double bond (CH3=CH2)

44. IUPAC Rules Name the longest chain.
Indicate the position of the double bond with the lowest number possible.
Substituent groups named like alkanes
5-methyl-2-hexene
                         

45. Name each of the following

46. Answers 6-dimethyl-2-heptene 2-ethyl-1-butene
4-ethyl-2-methyl-2-hexene
1-methylcyclohexene
2,4,4-trimethyl-2-pentene

47. Draw the structure for the following
3,4-dimethyl-2-pentene
3-ethyl-2-methyl-1-hexene
3-isopropylcyclopentene

48. Answers A. B. C.

49. Sec. 13.8 Properties of Alkenes
Objectives
Determine the properties of alkenes

50. Properties of Alkenes Similar to alkanes Occur widely in nature
Ethylene
Triggers fruit ripening
Can be used artifically
Others
Carotene
Vitamin A
Fruit coloring

51. Sec. 13.9 Chemical Properties: Reactions of Alkenes
Define addition reactions
Discuss hydrogenation and hydration
Write equations for reactions between alkenes and other substances

52. Addition Reactions
One of the bonds in the double bond is broken and each of the involved carbon atoms then bonds to another atom or group
Hydrogenation—addition of hydrogen to an unsaturated molecule

53. Halogen addition
Alkenes readily add halogen molecules

54. Hydration
Addition of water to an alkene

55. Equations
Write equations for the reaction between CH3CH=CHCH3 and each of the following H2
Br2
H2O (H2SO4 catalyst)

56. Answers

57. Write equations for the reaction of with each of the following.
H2 (Ni catalyst)
Cl2
H2O (H2SO4 catalyst)

58. Answers .

59. Sec Alkynes
Define alkyne
Name alkynes using IUPAC naming rules

60. Alkynes Carbon atoms share 3 pairs of electrons, forming a triple bond
Acetylene
Alkynes have similar properties to those of alkanes and alkenes
Naming is the same, except they end in
-yne

61. Sec. 13.12 Benzene Objectives
Recognize the versatile structure of a benzene ring

62. Benzene Recognized by Michael Faraday in 1825
Six sided structure with single and double mobile bonds
Resonance—a word used to describe the phenomenon in which no single Lewis structure can be used
Figure    

63. Sec. 13.13 Structure and Nomenclature of Aromatic Compounds
Define and name aromatic hydrocarbons and aliphatic compounds
Determine the difference between ortho, meta, and para distribution

64. Aromatic Compounds Benzene Named because thought to have strong aroma
Now define as anything that has a benzene ring
Aliphatic compounds—nonaromatic

65. Naming
One substituent…easy

66. Naming 2 substituents…2 different ways One way…same as before
Other way…uses the terms ortho, meta, and para
Ortho (1,2 distribution)
Meta (1,3 distribution)
Para (1,4 distribution)

67. Examples

68. Aryl Groups Sometimes Benzene rings attach to alkanes or alkenes
Known as aryl groups
Most common one is phenyl

69. Sec. 13.14 Uses of Benzene and Benzene Derivatives
Objectives
Discuss some of the uses of benzene

70. Uses of Benzene Most comes from petroleum Used as a starting material
Added to fuels to improve octane rating
Cigarette smoke
Very toxic
In Nature..
Tryptophan
Vitamin K
Folic acid
Many drugs…Table 13.12